Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry

Raffaele Senatore; Laura Castoldi; Laura Ielo; Wolfgang Holzer; Vittorio Pace

doi:10.1021/acs.orglett.8b00896

Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry

Raffaele Senatore, Laura Castoldi, Laura Ielo, Wolfgang Holzer, Vittorio Pace (Corresponding author)

Publications: Contribution to journal › Article › Peer Reviewed

Abstract

Diselenoacetals, previously considered byproducts in homologation tactics en route to α-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prep. α-aryl- and α-alkyl seleno methylketones through a single chem. operation. No racemization events are obsd. in the presence of optically pure starting materials.

Original language	English
Pages (from-to)	2685-2688
Number of pages	4
Journal	Organic Letters
Volume	20
Issue number	9
DOIs	https://doi.org/10.1021/acs.orglett.8b00896
Publication status	Published - 4 May 2018

Austrian Fields of Science 2012

104015 Organic chemistry

Keywords

AMIDES
ELIMINATION
KETONES
OLEFINS
ORGANOSELENIUM CHEMISTRY
REACTIVITY
REAGENTS
SELENIUM
SELENOESTERS
SELENOXIDES

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title = "Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry",

abstract = "Diselenoacetals, previously considered byproducts in homologation tactics en route to α-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prep. α-aryl- and α-alkyl seleno methylketones through a single chem. operation. No racemization events are obsd. in the presence of optically pure starting materials.",

keywords = "AMIDES, ELIMINATION, KETONES, OLEFINS, ORGANOSELENIUM CHEMISTRY, REACTIVITY, REAGENTS, SELENIUM, SELENOESTERS, SELENOXIDES",

author = "Raffaele Senatore and Laura Castoldi and Laura Ielo and Wolfgang Holzer and Vittorio Pace",

note = "Publisher Copyright: {\textcopyright} 2018 American Chemical Society.",

year = "2018",

month = may,

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doi = "10.1021/acs.orglett.8b00896",

language = "English",

volume = "20",

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journal = "Organic Letters",

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publisher = "AMER CHEMICAL SOC",

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TY - JOUR

T1 - Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry

AU - Senatore, Raffaele

AU - Castoldi, Laura

AU - Ielo, Laura

AU - Holzer, Wolfgang

AU - Pace, Vittorio

PY - 2018/5/4

Y1 - 2018/5/4

N2 - Diselenoacetals, previously considered byproducts in homologation tactics en route to α-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prep. α-aryl- and α-alkyl seleno methylketones through a single chem. operation. No racemization events are obsd. in the presence of optically pure starting materials.

AB - Diselenoacetals, previously considered byproducts in homologation tactics en route to α-selenoketones, are herein found to be excellent starting materials for this purpose. The easy selenium/lithium exchange they undergo affords seleno carbanions which are smoothly added to Weinreb amides to chemoselectively prep. α-aryl- and α-alkyl seleno methylketones through a single chem. operation. No racemization events are obsd. in the presence of optically pure starting materials.

KW - AMIDES

KW - ELIMINATION

KW - KETONES

KW - OLEFINS

KW - ORGANOSELENIUM CHEMISTRY

KW - REACTIVITY

KW - REAGENTS

KW - SELENIUM

KW - SELENOESTERS

KW - SELENOXIDES

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U2 - 10.1021/acs.orglett.8b00896

DO - 10.1021/acs.orglett.8b00896

M3 - Article

C2 - 29664309

SN - 1523-7060

VL - 20

SP - 2685

EP - 2688

JO - Organic Letters

JF - Organic Letters

IS - 9

ER -

Expeditious and Chemoselective Synthesis of α-Aryl and α-Alkyl Selenomethylketones via Homologation Chemistry

Abstract

Austrian Fields of Science 2012

Keywords

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